Palladium-Catalyzed Decarboxylative Formal (4+2) Cycloaddition of Vinyl Benzoxazinanones with 3-Nitroindoles

Abstract A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H -indolo[2,3- b ]quinolines in excellent yield (up to 94%) and diastereoselectivity...

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Bibliographic Details
Published in:Synlett 2020-06, Vol.31 (9), p.916-924
Main Authors: Bird, Melissa J., Wales, Steven M., Richardson, Christopher, Hyland, Christopher J. T.
Format: Article
Language:English
Subjects:
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Summary:Abstract A diastereoselective palladium-catalyzed dearomative formal (4 + 2) cycloaddition between vinyl benzoxazinanones and 3-nitroindoles has been developed. This reaction provides a concise route to tetrahydro-5 H -indolo[2,3- b ]quinolines in excellent yield (up to 94%) and diastereoselectivity (up to >98:2), with versatile functional handles including vinyl, nitro, and free NH groups.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0040-1707995